JPH1059984A - Oligomer mixture of condensed alkyl alkoxysilane - Google Patents
Oligomer mixture of condensed alkyl alkoxysilaneInfo
- Publication number
- JPH1059984A JPH1059984A JP9158276A JP15827697A JPH1059984A JP H1059984 A JPH1059984 A JP H1059984A JP 9158276 A JP9158276 A JP 9158276A JP 15827697 A JP15827697 A JP 15827697A JP H1059984 A JPH1059984 A JP H1059984A
- Authority
- JP
- Japan
- Prior art keywords
- oligomer mixture
- group
- condensed
- alkyl
- oligomer
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 39
- 125000000217 alkyl group Chemical group 0.000 title claims abstract description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 21
- 238000004821 distillation Methods 0.000 claims abstract description 11
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 11
- 230000007062 hydrolysis Effects 0.000 claims abstract description 10
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 9
- 239000011541 reaction mixture Substances 0.000 claims abstract description 9
- 239000003054 catalyst Substances 0.000 claims abstract description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims abstract description 6
- 238000009833 condensation Methods 0.000 claims abstract description 4
- 230000005494 condensation Effects 0.000 claims abstract description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 238000006384 oligomerization reaction Methods 0.000 claims description 5
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 229910000077 silane Inorganic materials 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000011261 inert gas Substances 0.000 claims description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 3
- 230000000694 effects Effects 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 238000007363 ring formation reaction Methods 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- MSRJTTSHWYDFIU-UHFFFAOYSA-N octyltriethoxysilane Chemical compound CCCCCCCC[Si](OCC)(OCC)OCC MSRJTTSHWYDFIU-UHFFFAOYSA-N 0.000 description 5
- 229960003493 octyltriethoxysilane Drugs 0.000 description 5
- -1 siloxanes Chemical class 0.000 description 4
- 238000010626 work up procedure Methods 0.000 description 4
- 238000006482 condensation reaction Methods 0.000 description 3
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000010445 mica Substances 0.000 description 2
- 229910052618 mica group Inorganic materials 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 239000012855 volatile organic compound Substances 0.000 description 2
- 229910052845 zircon Inorganic materials 0.000 description 2
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 2
- 239000004971 Cross linker Substances 0.000 description 1
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- RREGISFBPQOLTM-UHFFFAOYSA-N alumane;trihydrate Chemical compound O.O.O.[AlH3] RREGISFBPQOLTM-UHFFFAOYSA-N 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000011449 brick Substances 0.000 description 1
- 239000004566 building material Substances 0.000 description 1
- ROPDWRCJTIRLTR-UHFFFAOYSA-L calcium metaphosphate Chemical compound [Ca+2].[O-]P(=O)=O.[O-]P(=O)=O ROPDWRCJTIRLTR-UHFFFAOYSA-L 0.000 description 1
- 239000004568 cement Substances 0.000 description 1
- 239000002734 clay mineral Substances 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 239000004567 concrete Substances 0.000 description 1
- WMWXXXSCZVGQAR-UHFFFAOYSA-N dialuminum;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3] WMWXXXSCZVGQAR-UHFFFAOYSA-N 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910000449 hafnium oxide Inorganic materials 0.000 description 1
- WIHZLLGSGQNAGK-UHFFFAOYSA-N hafnium(4+);oxygen(2-) Chemical compound [O-2].[O-2].[Hf+4] WIHZLLGSGQNAGK-UHFFFAOYSA-N 0.000 description 1
- XNQAOQBTOJDMEA-UHFFFAOYSA-N hafnium(4+);oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[Hf+4] XNQAOQBTOJDMEA-UHFFFAOYSA-N 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- NDLPOXTZKUMGOV-UHFFFAOYSA-N oxo(oxoferriooxy)iron hydrate Chemical compound O.O=[Fe]O[Fe]=O NDLPOXTZKUMGOV-UHFFFAOYSA-N 0.000 description 1
- KGQGQKPCLGRZAZ-UHFFFAOYSA-N oxocobalt;hydrate Chemical compound O.[Co]=O KGQGQKPCLGRZAZ-UHFFFAOYSA-N 0.000 description 1
- IYVLHQRADFNKAU-UHFFFAOYSA-N oxygen(2-);titanium(4+);hydrate Chemical compound O.[O-2].[O-2].[Ti+4] IYVLHQRADFNKAU-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000004808 supercritical fluid chromatography Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229920002397 thermoplastic olefin Polymers 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- LRXTYHSAJDENHV-UHFFFAOYSA-H zinc phosphate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LRXTYHSAJDENHV-UHFFFAOYSA-H 0.000 description 1
- 229910000165 zinc phosphate Inorganic materials 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2/00—Processes or devices for granulating materials, e.g. fertilisers in general; Rendering particulate materials free flowing in general, e.g. making them hydrophobic
- B01J2/30—Processes or devices for granulating materials, e.g. fertilisers in general; Rendering particulate materials free flowing in general, e.g. making them hydrophobic using agents to prevent the granules sticking together; Rendering particulate materials free flowing in general, e.g. making them hydrophobic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0838—Compounds with one or more Si-O-Si sequences
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/21—Cyclic compounds having at least one ring containing silicon, but no carbon in the ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/045—Polysiloxanes containing less than 25 silicon atoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/04—Polysiloxanes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Silicon Polymers (AREA)
Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、鎖式及び／又は環
式縮合されたアルキルアルコキシシランのオリゴマー混
合物、その製法及びその使用に関する。The present invention relates to oligomeric mixtures of linear and / or cyclically condensed alkylalkoxysilanes, to a process for their preparation and to their use.
【０００２】[0002]
【従来の技術】アルキルトリアルコキシシランは、加水
分解の際に、アルコールを遊離する。量にして、例え
ば、オクチルトリエトキシシランでのこの加水分解アル
コールは、使用トリアルコキシシランの約５０重量％で
ある。従って、多くの使用が、アルキルトリアルコキシ
シランに関して閉ざされたままであるか、又はこのこと
により、例えば、必要な爆発防止又は経済的な理由か
ら、悪影響を受けている−略語：ＶＯＣ＝揮発性有機化
合物。しかし、使用技術的観点から往々にして、純粋な
アルキルトリアルコキシシランの特性に似た特性を有す
るが、前記の欠点を甘受する必要の無い物質を使用可能
にすることが、望ましいと思われる。このような物質
は、殊に、無機表面の疎水化の際に使用することができ
る。2. Description of the Prior Art Alkyl trialkoxysilanes release alcohol upon hydrolysis. In quantity, for example, this hydrolyzed alcohol in octyltriethoxysilane is about 50% by weight of the trialkoxysilane used. Thus, many uses remain closed for alkyltrialkoxysilanes or are thereby adversely affected, for example, for necessary explosion protection or for economic reasons-abbreviation: VOC = volatile organic Compound. However, it will often be desirable from a technical point of view to be able to use substances which have properties similar to those of pure alkyltrialkoxysilanes, but which do not have to accept the disadvantages mentioned above. Such substances can be used in particular for hydrophobizing inorganic surfaces.
【０００３】ヨーロッパ特許出願第０５１８０５７号明
細書出願から、オリゴマー化度０〜８を有するシロキサ
ンオリゴマーの混合物が公知であり、その際、このシロ
キサンは、Ｓｉ−原子１個当たり、せいぜい１個のビニ
ル基並びにメトキシ基もしくはエトキシ基及び場合によ
り１〜１８個のＣ−原子を有するアルキル基を含有す
る。更に、ヨーロッパ特許（ＥＰ−Ａ）第０５１８１０
５７Ａ１号明細書は、このシロキサン混合物の製法を開
示している。その官能化により、ビニル基を特徴とする
このシロキサン混合物は、殊に、熱可塑性ポリオレフィ
ンをベースとするケーブル材料を製造する際の架橋剤と
して、かつ架橋可能な有機物質との相互作用での同様の
使用で好適である。[0003] From European Patent Application No. 0 518 057, mixtures of siloxane oligomers having a degree of oligomerization of 0 to 8 are known, the siloxanes containing at most one vinyl compound per Si atom. It contains methoxy or ethoxy groups and optionally alkyl groups having 1 to 18 C-atoms. Further, European Patent No. 051810
57A1 discloses a process for preparing this siloxane mixture. Due to its functionalization, this siloxane mixture, characterized by vinyl groups, is particularly useful as a crosslinker in the production of cable materials based on thermoplastic polyolefins and in the interaction with crosslinkable organic substances. It is suitable for use.
【０００４】[0004]
【発明が解決しようとする課題】本発明の課題は、殊
に、無機表面上に塗布して、親水性液体、例えば水によ
り無機表面が濡れることを充分に防ぐ、即ち、無機表面
を疎水化するのに適当で、かつ無機表面上に施与する
と、同様の条件下で濃縮された形のアルキルトリアルコ
キシシランを使用した場合に比べて、水の添加下にかな
りより少ないアルコールを遊離する液体を提供すること
である。The object of the present invention is, in particular, to apply sufficiently to an inorganic surface to sufficiently prevent the inorganic surface from being wetted by a hydrophilic liquid, for example water, ie to render the inorganic surface hydrophobic. Liquid that, when applied to an inorganic surface, is capable of releasing significantly less alcohol with the addition of water than when using an alkyltrialkoxysilane in a concentrated form under similar conditions. It is to provide.
【０００５】[0005]
【課題を解決するための手段】記載の課題は、本発明に
より、請求項の記載に相応して解決される。The object of the invention is achieved according to the invention in accordance with the claims.
【０００６】さて、例えば、オクチルトリエトキシシラ
ンから、酸性触媒の存在下での調節された加水分解反応
及び縮合反応及び後続の、減圧下での加水分解アルコー
ルの蒸留による除去により（この際、反応混合物の蒸留
による後処理を、充分に穏やかな条件下で行う）、オク
チルエトキシシロキサンの低粘度混合物が得られ、この
際、エトキシ基の含有率は、２０重量％未満であり、か
つ遊離のエタノールの含有率は、１．５重量％未満であ
り、かつ１２５℃の引火点を有する；比較：純粋なオク
チルトリエトキシシランは、１０９℃の引火点を有す
る。更に、本発明のオリゴマー混合物は、有利な方法
で、無機表面を疎水化するために好適であり、その際、
濃縮された形のアルキルトリアルコキシシランの使用と
比較して、多量のアルコールが加水分解で遊離されるこ
とは無い。Now, for example, from octyltriethoxysilane, a controlled hydrolysis and condensation reaction in the presence of an acidic catalyst and subsequent removal of the hydrolyzed alcohol under reduced pressure by distillation. The work-up by distillation of the mixture is carried out under sufficiently mild conditions) to give a low-viscosity mixture of octylethoxysiloxanes, the content of ethoxy groups being less than 20% by weight and free ethanol being present. Is less than 1.5% by weight and has a flash point of 125 ° C .; comparison: pure octyltriethoxysilane has a flash point of 109 ° C. Furthermore, the oligomer mixtures according to the invention are suitable for hydrophobizing inorganic surfaces in an advantageous manner, wherein
Compared to the use of the alkyltrialkoxysilane in concentrated form, no large amounts of alcohol are liberated by hydrolysis.
【０００７】従って、本発明の目的は、鎖式及び／又は
環式縮合されたアルキルアルコキシシランのオリゴマー
混合物であり、それは、このオリゴマー混合物が、２重
量％未満の遊離アルコールを含有し、かつこの縮合され
たアルコキシシランが、一般式Ｉ：[0007] An object of the present invention is therefore an oligomer mixture of linear and / or cyclically condensed alkylalkoxysilanes, which oligomer mixture contains less than 2% by weight of free alcohol and The condensed alkoxysilane has the general formula I:
【０００８】[0008]
【化３】 Embedded image
【０００９】[式中、Ｒは、３〜１８個のＣ原子、有利
に４〜１６個のＣ−原子、特に有利に６〜１０個のＣ−
原子を有するアルキルであり、Ｒ′は、メチル基又はエ
チル基又は水素原子並びにメチル基又は水素原子並びに
エチル基であり、オリゴマー化度は、２≦ｘ≦２０の範
囲であり、かつモル比[Ｓｉ／アルコキシ−基]の商は、
≧１である]及び／又は一般式ＩＩ：Wherein R is 3 to 18 C atoms, preferably 4 to 16 C atoms, particularly preferably 6 to 10 C atoms.
R ′ is a methyl or ethyl group or a hydrogen atom and a methyl or hydrogen atom and an ethyl group, the degree of oligomerization is in the range of 2 ≦ x ≦ 20, and the molar ratio [ The quotient of Si / alkoxy-group] is
≧ 1] and / or general formula II:
【００１０】[0010]
【化４】 Embedded image
【００１１】[式中、Ｒは、３〜１８個のＣ原子、有利
に４〜１６個のＣ−原子、特に有利に６〜１０個のＣ−
原子を有するアルキルであり、Ｒ′は、メチル基又はエ
チル基又は水素原子並びにメチル基又は水素原子並びに
エチル基であり、ｘ≧３のオリゴマー化度であり、かつ
モル比[Ｓｉ／アルコキシ−基]の商は、≧１である]に
相当することを特徴とする。Wherein R is 3 to 18 C atoms, preferably 4 to 16 C atoms, particularly preferably 6 to 10 C atoms.
R ′ is a methyl or ethyl group or a hydrogen atom and a methyl or hydrogen atom and an ethyl group, has a degree of oligomerization of x ≧ 3, and has a molar ratio of [Si / alkoxy-group The quotient of] is ≧ 1].
【００１２】本発明のオリゴマー混合物は、０．０１重
量％を上回り、かつ２０重量％を下回る（これらの値
は、それぞれ、前記のオリゴマー混合物の重量に対す
る）アルコキシ基含有率を有するのが有利である。The oligomer mixture according to the invention advantageously has an alkoxy group content of more than 0.01% by weight and less than 20% by weight (these values are each based on the weight of said oligomer mixture). is there.
【００１３】更に、本発明のオリゴマー混合物は、一般
式中でＲとして表される、それぞれ同じ鎖長を有するア
ルキル基を有するのが有利である。殊に、Ｒは、オクチ
ル基である。Furthermore, the oligomer mixture according to the invention advantageously has alkyl radicals, each represented by the general formula R, having the same chain length. In particular, R is an octyl group.
【００１４】本発明のオリゴマー混合物は、１００ｍＰ
ａ・ｓ未満の粘度を有するのが有利である。The oligomer mixture of the present invention has a viscosity of 100 mP.
It is advantageous to have a viscosity of less than a · s.
【００１５】更に、本発明の目的は、使用シランが、３
〜１８個のＣ−原子を有するアルキル基及びアルコキシ
基としてのメトキシ及び／又はエトキシ基を有するアル
キルトリアルコキシシランを、Ｓｉ１モル当たり１モル
を上回る水の使用下に、かつ触媒としてのＨＣｌの使用
下に加水分解及び縮合し、得られた反応混合物を、減圧
下、９５℃未満の缶温度(Sumpftemperatur)で蒸留によ
り後処理することによる、請求項１に記載のオリゴマー
混合物の製法である。Further, an object of the present invention is that the silane used is 3
Use of alkyltrialkoxysilanes having methoxy and / or ethoxy groups as alkyl and alkoxy groups having -18 C-atoms with the use of more than 1 mole of water per mole of Si and use of HCl as catalyst The process according to claim 1, wherein the mixture is hydrolyzed and condensed, and the reaction mixture obtained is worked up by distillation under reduced pressure at a can temperature of less than 95 ° C. (Sumpftemperatur).
【００１６】本発明の方法では、使用アルキルトリアル
コキシシランの加水分解及び縮合を、希釈剤並びに溶剤
としてメタノール及び／又はエタノールを使用して実施
するのが好適である。溶剤の量を、通常、単相混合物が
生ずるように選択する。In the process according to the invention, the hydrolysis and condensation of the alkyltrialkoxysilanes used are preferably carried out using methanol and / or ethanol as diluent and solvent. The amount of solvent is usually chosen such that a single-phase mixture results.
【００１７】オクチルトリエトキシシランの加水分解の
ために、本発明の方法では、例えば、シラン１モル当た
り水１．２モルを使用することができる。For the hydrolysis of octyltriethoxysilane, for example, 1.2 mol of water per mol of silane can be used in the process according to the invention.
【００１８】本発明の方法では通常、反応混合物の後続
蒸留後処理で、再び、ほぼ定量的に除去することができ
る加水分解触媒として、ＨＣｌを使用するのが有利であ
る。しかし、その他の酸を触媒として使用することもで
きる。In the process according to the invention, it is usually advantageous to use HCl as a hydrolysis catalyst which can be removed again almost quantitatively in the subsequent distillation work-up of the reaction mixture. However, other acids can be used as catalysts.
【００１９】加水分解反応及び縮合反応を、本発明の方
法では、通常、穏やかに、１０〜８０℃、特に３０〜７
８℃の範囲の温度で実施するのが有利である。反応は、
保護ガス下でも実施することができる。更に、反応を、
常圧下に実施するのが適当である。In the method of the present invention, the hydrolysis reaction and the condensation reaction are usually carried out gently at 10 to 80 ° C., especially 30 to 7 ° C.
It is advantageous to carry out at a temperature in the range of 8 ° C. The reaction is
It can also be carried out under protective gas. In addition, the reaction
It is suitably carried out under normal pressure.
【００２０】加水分解反応及び縮合反応を、本発明の方
法では、撹拌下に、１〜２時間かけて実施するのが有利
である。In the process of the present invention, the hydrolysis and condensation reactions are advantageously carried out under stirring for 1 to 2 hours.
【００２１】こうして得られた反応混合物を、本発明の
方法では蒸留により、減圧下に後処理する。その際、同
じく充分に穏やかな条件下で、遊離のアルコール量の大
部分の除去を行い、好適には、同時に触媒成分も一緒に
排出させる。この蒸留による後処理では、缶温度は、殊
に、９０℃を上回るべきではない。反応混合物を、不活
性ガス流、例えば窒素の供給下に、後処理するのが有利
である。蒸留による後処理の残留物として、本発明の生
成物が、澄明な低粘度の液体として得られる。The reaction mixture thus obtained is worked up under reduced pressure by distillation in the process according to the invention. In this case, the removal of the majority of the free alcohol is carried out, again under sufficiently mild conditions, and preferably the catalyst component is simultaneously discharged. In this work-up by distillation, the can temperature should in particular not exceed 90 ° C. The reaction mixture is advantageously worked up under a stream of inert gas, for example nitrogen. As a residue of the work-up by distillation, the product according to the invention is obtained as a clear, low-viscosity liquid.
【００２２】本発明のオリゴマー混合物の特別な利点
は、その引火点が、相応する純粋なアルキルトリアルコ
キシシラン又はそのアルコール溶液の引火点を上回るこ
とでもある。例えば、本発明のオリゴマー混合物の引火
点は、１００℃、特に１１０℃を上回るのが有利であ
る。A particular advantage of the oligomer mixture according to the invention is also that its flash point is above that of the corresponding pure alkyltrialkoxysilane or its alcoholic solution. For example, the flash point of the oligomer mixture according to the invention is advantageously above 100 ° C., in particular above 110 ° C.
【００２３】更に、本発明の目的は、請求項１に記載の
本発明のオリゴマー混合物又は請求項７により製造され
るオリゴマー混合物を、無機表面の疎水化のために使用
することである。It is a further object of the present invention to use the oligomer mixture of the invention according to claim 1 or the oligomer mixture prepared according to claim 7 for hydrophobizing inorganic surfaces.
【００２４】このような無機表面を有する物質は、例え
ば次のものである：建材、例えば、コンクリート、セメ
ント、モルタル、漆喰砂岩、レンガ又は天然石の種々の
もの、更に、無機粉末、例えば、慣用の填料又は顔料、
酸化アルミニウム又は酸化アルミニウム水和物、例え
ば、アルミニウム三水和物、ケイ酸、石英、雲母、酸化
チタン、酸化ジルコン、酸化ハフニウム又は酸化チタン
水和物、酸化ジルコン水和物、酸化ハフニウム水和物、
酸化鉄もしくは酸化鉄水和物又はコバルトもしくは酸化
コバルト水和物、更に、漆喰及び粘度鉱物並びに雲母鉄
鋼、タルク、リン酸亜鉛及びメタリン酸カルシウム。Substances having such an inorganic surface are, for example, the following: building materials, such as concrete, cement, mortar, stucco sandstone, bricks or natural stones, and also inorganic powders, such as customary Filler or pigment,
Aluminum oxide or aluminum oxide hydrate, for example, aluminum trihydrate, silicic acid, quartz, mica, titanium oxide, zircon oxide, hafnium oxide or titanium oxide hydrate, zircon oxide hydrate, hafnium oxide hydrate ,
Iron oxide or iron oxide hydrate or cobalt or cobalt oxide hydrate, as well as stucco and clay minerals, and mica steel, talc, zinc phosphate and calcium metaphosphate.
【００２５】本発明のオリゴマー混合物を、疎水特性を
有する無機物質の製造の際に、殊に、有利には、酸化中
間相、殊に、酸化ケイ素層及び／又は酸化アルミニウム
層の施与後の粉末物質のために、使用するのが好適であ
る。The oligomer mixtures according to the invention can be used in the preparation of inorganic substances having hydrophobic properties, in particular after the application of an oxidized mesophase, in particular a silicon oxide layer and / or an aluminum oxide layer. For powdery substances, it is preferred to use.
【００２６】[0026]
【実施例】本発明を次の例で詳述する： 例 真空装置、配量装置及び蒸留装置並びに窒素供給管を有
する４ｌガラス製撹拌反応器中に、オクチルトリエトキ
シシラン２２０８ｇを予め装入し、引き続き、３２重量
％ＨＣｌ水溶液６．９ｇ及びエタノール４００ｇと予め
混合された水１６８ｇを、３０〜７０℃で常圧下に配量
導入する。澄明な混合物を、約７７℃に、弱い還流下
に、約２時間保持する。澄明な反応混合物が生じる。引
き続き、４００ミリバールから約５ミリバールまでに低
下する圧力での真空及び９５℃未満の缶温度の適用下
に、同時に窒素流を供給して、エタノールを留去する
（約７時間）。次の特性を有する生成物１５５０ｇを単
離する。The invention is explained in more detail in the following examples: Example 2208 g of octyltriethoxysilane are pre-charged in a stirred 4 l glass reactor equipped with a vacuum, metering and distillation apparatus and a nitrogen supply. Subsequently, 6.9 g of a 32% by weight aqueous HCl solution and 168 g of water previously mixed with 400 g of ethanol are metered in at 30 to 70 ° C. under normal pressure. The clear mixture is kept at about 77 ° C. under a slight reflux for about 2 hours. A clear reaction mixture results. Subsequently, a stream of nitrogen is fed in simultaneously with the application of a vacuum at a pressure falling from 400 mbar to about 5 mbar and a can temperature of less than 95 ° C. to distill off the ethanol (about 7 hours). 1550 g of product having the following properties are isolated.
【００２７】遊離のエタノール（ガスクロマトグラフィ
ーによる）：１．３重量％ Ｓｉ１モルあたりエトキシ基０．８モル（1Ｈ−ＮＭ
Ｒ） 粘度：３８．８ｍＰａ・ｓ（ＤＩＮ５３０１５） 沸点：２８０℃ 引火点：１２５℃ 密度：０．９５ｇ／ｍｌ Ｃｌ−含有率：６６重量ｐｐｍ オリゴマー化度：３〜２０、平均モル量１１６０ｇ／モ
ル（ＧＰＣ、即ち、ゲル浸透クロマトグラフィー、ＳＦ
Ｃ、即ち、超臨界流体クロマトグラフィー）。The free ethanol (by gas chromatography): 1.3 wt% Si1 per mole ethoxy 0.8 mole (1 H-NM
R) Viscosity: 38.8 mPa · s (DIN 53015) Boiling point: 280 ° C. Flash point: 125 ° C. Density: 0.95 g / ml Cl—content: 66 wt ppm Oligomerization degree: 3-20, average molar amount 1160 g / mol (GPC, gel permeation chromatography, SF
C, ie supercritical fluid chromatography).
───────────────────────────────────────────────────── フロントページの続き (72)発明者 アルベルト フリングス ドイツ連邦共和国 ラインフェルデン デ ューラーシュトラーセ 48 (72)発明者 ミヒャエル ホルン ドイツ連邦共和国 ラインフェルデン マ イゼンライン 11 (72)発明者 ペーター イェンクナー ドイツ連邦共和国 ラインフェルデン フ リードリッヒ−エーベルト−シュトラーセ ８／22 (72)発明者 ラルフ ラーフェン ドイツ連邦共和国 ニーダードッセンバッ ハ タールマットシュトラーセ 16 (72)発明者 ヤロスラフ モンキーヴィチュ ドイツ連邦共和国 ラインフェルデン ブ ルステルシュトラーセ ２ アー ──────────────────────────────────────────────────続 き Continued on the front page (72) Inventor Albert Frings Rheinfelden-de-Ultrastrasse 48 Germany (72) Inventor Michael Horn Rheinfelden Meisenlein Germany 11 (72) Inventor Peter Jenkner Germany Republic Rheinfelden-Friedrich-Ebelt-Strasse 8/22 (72) Inventor Ralph Rafen Germany Niederdossenbach-Hartmatstraße 16 (72) Inventor Yaroslav Monkeyvich Germany Rheinfelden-Bulsterstrasse 2 Ah
Claims (12)
縮合されていてよいアルキルアルコキシシランからなる
オリゴマー混合物において、このオリゴマー混合物は、
２重量％未満の遊離アルコールを含有し、かつこの縮合
アルコキシシランは、一般式Ｉ： 【化１】 [式中、Ｒは、３〜１８個のＣ原子を有するアルキルで
あり、 Ｒ′は、メチル基又はエチル基又は水素原子並びにメチ
ル基又は水素原子並びにエチル基であり、 オリゴマー化度は、２≦ｘ≦２０の範囲であり、かつモ
ル比[Ｓｉ／アルコキシ−基]の商は、≧１である]及び
／又は一般式ＩＩ： 【化２】 [式中、Ｒは、３〜１８個のＣ原子を有するアルキル基
であり、 Ｒ′は、メチル基又はエチル基又は水素原子並びにメチ
ル基又は水素原子並びにエチル基であり、 ｘ≧３のオリゴマー化度であり、かつモル比[Ｓｉ／ア
ルコキシ−基]の商は、≧１である]に相当する、一様
に、又は種々に、かつ鎖状又は環状縮合されていてよい
アルキルアルコキシシランからなるオリゴマー混合物。1. An oligomer mixture consisting of alkylalkoxysilanes which may be homogeneously or variously and which may be chain- or cyclic-condensed, wherein the oligomer mixture comprises:
It contains less than 2% by weight of free alcohol and the condensed alkoxysilane has the general formula I: Wherein R is an alkyl having 3 to 18 C atoms, R ′ is a methyl group or an ethyl group or a hydrogen atom and a methyl group or a hydrogen atom and an ethyl group, and the degree of oligomerization is 2 ≦ x ≦ 20 and the quotient of the molar ratio [Si / alkoxy-group] is ≧ 1] and / or the general formula II: Wherein R is an alkyl group having 3 to 18 C atoms, R ′ is a methyl group or an ethyl group or a hydrogen atom, and a methyl group or a hydrogen atom and an ethyl group, and x ≧ 3 oligomers , And the quotient of the molar ratio [Si / alkoxy-group] is ≧ 1], from alkylalkoxysilanes, which may be linearly or cyclically and condensed, Oligomer mixture.
混合物の重量に対して、０．０１重量％を上回り、かつ
２０重量％を下回るである、請求項１に記載のオリゴマ
ー混合物。2. The oligomer mixture according to claim 1, wherein the content of alkoxy groups is greater than 0.01% by weight and less than 20% by weight, based on the weight of the oligomer mixture.
るアルキル基である、請求項１又は２に記載のオリゴマ
ー混合物。3. The oligomer mixture according to claim 1, wherein R is an alkyl group having the same number of C-atoms.
載のオリゴマー混合物。4. The oligomer mixture according to claim 3, wherein R is an octyl group.
請求項１から４のいずれかに記載のオリゴマー混合物。5. The composition has a viscosity of less than 100 mPa · s.
An oligomer mixture according to any one of claims 1 to 4.
から５のいずれかに記載のオリゴマー混合物。6. The method according to claim 1, wherein the flash point is higher than 100 ° C.
6. The oligomer mixture according to any one of claims 1 to 5.
法において、使用シランが、３〜１８個のＣ−原子を有
するアルキル基及びアルコキシ基としてのメトキシ及び
／又はエトキシ基を有するアルキルトリアルコキシシラ
ンを、Ｓｉ１モル当たり１モルを上回る水の使用下に、
かつ触媒としてのＨＣｌの使用下に加水分解及び縮合
し、かつ得られた反応混合物を、減圧下、９５℃未満の
缶温度で蒸留により後処理することを特徴とする、請求
項１に記載のオリゴマー混合物の製法。7. The process for producing an oligomer mixture according to claim 1, wherein the silane used is an alkyltrialkoxysilane having an alkyl group having 3 to 18 C-atoms and a methoxy and / or ethoxy group as an alkoxy group. With the use of more than 1 mole of water per mole of Si,
2. The process according to claim 1, wherein the reaction mixture is hydrolyzed and condensed using HCl as a catalyst, and the reaction mixture obtained is worked up by distillation under reduced pressure at a bottom temperature of less than 95.degree. Preparation of oligomer mixture.
水分解及び縮合を、希釈剤並びに溶剤としてメタノール
及び／又はエタノールを使用して実施する、請求項７に
記載の方法。8. The process as claimed in claim 7, wherein the hydrolysis and condensation of the alkyltrialkoxysilane used are carried out using methanol and / or ethanol as diluent and solvent.
水分解及び縮合を、１０〜８０℃の温度で、常圧下に実
施する、請求項７又は８に記載の方法。9. The process according to claim 7, wherein the hydrolysis and condensation of the alkyltrialkoxysilane used are carried out at a temperature of from 10 to 80 ° C. under normal pressure.
に後処理する、請求項７から９のいずれかに記載の方
法。10. The process as claimed in claim 7, wherein the reaction mixture is worked up in a stream of an inert gas.
項７により製造されたオリゴマー混合物を、無機表面の
疎水化のために使用すること。11. Use of the oligomer mixture according to claim 1 or the oligomer mixture prepared according to claim 7 for hydrophobizing inorganic surfaces.
を、粉末物質の疎水化のために使用すること。12. Use of the oligomer mixture according to claim 11 for hydrophobizing powdered substances.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19624032A DE19624032A1 (en) | 1996-06-17 | 1996-06-17 | Oligomer mixture of condensed alkylalkoxysilanes |
| DE19624032.8 | 1996-06-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH1059984A true JPH1059984A (en) | 1998-03-03 |
Family
ID=7797109
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9158276A Pending JPH1059984A (en) | 1996-06-17 | 1997-06-16 | Oligomer mixture of condensed alkyl alkoxysilane |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US5932757A (en) |
| EP (1) | EP0814110B1 (en) |
| JP (1) | JPH1059984A (en) |
| CA (1) | CA2207977A1 (en) |
| DE (2) | DE19624032A1 (en) |
| PL (1) | PL320584A1 (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2000178449A (en) * | 1998-10-27 | 2000-06-27 | Degussa Huels Ag | Aminopropyl-functional siloxane oligomer |
| JP2006507375A (en) * | 2002-08-22 | 2006-03-02 | デグサ アクチエンゲゼルシャフト | Acts as a coupling agent for filled and peroxide crosslinked rubber compounds |
| JP2008537740A (en) * | 2005-03-24 | 2008-09-25 | 株式会社ブリヂストン | Silica-reinforced rubber compounding with low emission of volatile organic compounds (VOC) |
| JP2013028530A (en) * | 2002-04-26 | 2013-02-07 | Evonik Degussa Gmbh | Process for impregnating porous mineral support, and use of specific spray technology therefor |
| US8962746B2 (en) | 2007-12-27 | 2015-02-24 | Bridgestone Corporation | Methods of making blocked-mercapto alkoxy-modified silsesquioxane compounds |
| US9365700B2 (en) | 2007-12-31 | 2016-06-14 | Bridgestone Corporation | Amino alkoxy-modified silsesquioxane adhesives for improved metal adhesion and metal adhesion retention to cured rubber |
| US11401440B2 (en) | 2014-12-31 | 2022-08-02 | Bridgestone Corporation | Amino alkoxy-modified silsesquioxane adhesives for adhering steel alloy to rubber |
Families Citing this family (73)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6140445A (en) | 1998-04-17 | 2000-10-31 | Crompton Corporation | Silane functional oligomer |
| DE19830128A1 (en) | 1998-07-06 | 2000-02-10 | Degussa | Surface modified flame retardants, processes for their production and their use |
| DE19834990B4 (en) * | 1998-08-03 | 2005-09-15 | Degussa Ag | Acryloxypropyl or methacryloxypropyl-containing siloxane oligomers, processes for their preparation and their use |
| DE19848351A1 (en) | 1998-10-21 | 2000-04-27 | Degussa | Camera with internal exposure function has controller that determines light output of light output device according to sensitivity of film determined by film sensitivity detector |
| US6541671B1 (en) | 2002-02-13 | 2003-04-01 | The Regents Of The University Of California | Synthesis of 2H- and 13C-substituted dithanes |
| JP2001114896A (en) * | 1999-10-13 | 2001-04-24 | Shin Etsu Chem Co Ltd | Method for producing terminal hydrolyzable group-blocked organopolysiloxane |
| EP1195416A3 (en) * | 2000-10-05 | 2005-12-28 | Degussa AG | Polymerisable silicone-organic nanocapsules |
| EP1195417B1 (en) | 2000-10-05 | 2009-10-14 | Evonik Degussa GmbH | Silicone-organic nanocapsules |
| DE10056344A1 (en) * | 2000-11-14 | 2002-05-16 | Degussa | n-Propylethoxysiloxanes, process for their preparation and their use |
| DE10056343A1 (en) | 2000-11-14 | 2002-05-16 | Degussa | Continuous process for the production of organoalkoxysiloxanes |
| DE10059468A1 (en) * | 2000-11-30 | 2001-11-15 | Wacker Chemie Gmbh | Organopolysiloxane resins which are readily soluble in liquid organopolysiloxane compounds, for use in all normal applications, are based on units with long-chain, silicon-carbon linked hydrocarbyl groups |
| DE10100384A1 (en) * | 2001-01-05 | 2002-07-11 | Degussa | Process for modifying the functionality of organofunctional substrate surfaces |
| EP1245627B1 (en) | 2001-03-30 | 2007-07-04 | Degussa GmbH | Organic silicon nano-microhybrid system or micro-hybrid system containing compositions for scratch and abrasion resistant coatings |
| EP1249470A3 (en) | 2001-03-30 | 2005-12-28 | Degussa AG | Highly filled pasty siliconorganic nano and/or microhybridcapsules containing composition for scratch and/or abrasion resistant coatings |
| DE10141687A1 (en) | 2001-08-25 | 2003-03-06 | Degussa | Agent for coating surfaces containing silicon compounds |
| DE10151264A1 (en) | 2001-10-17 | 2003-04-30 | Degussa | Aminoalkylalkoxysiloxane-containing mixtures, their preparation and their use |
| DE10153803A1 (en) | 2001-11-05 | 2003-05-15 | Degussa | Corrosion inhibitor for reinforced concrete |
| DE10212523A1 (en) | 2002-03-21 | 2003-10-02 | Degussa | Air-drying, silane-containing coating agents |
| DE10240756A1 (en) | 2002-08-30 | 2004-03-11 | Degussa Ag | Desiccant containing alkoxysiloxane for cross-linkable polymer compositions |
| DE10321320A1 (en) * | 2003-05-13 | 2004-12-02 | Degussa Ag | Organofunctional siloxane mixtures |
| DE10330020A1 (en) * | 2003-07-03 | 2005-01-20 | Degussa Ag | Highly filled silane preparation |
| DE10336544A1 (en) * | 2003-08-05 | 2005-02-24 | Degussa Ag | Two-component coating system for smooth surfaces with "easy-to-clean" properties |
| DE10362060B4 (en) * | 2003-10-21 | 2009-07-09 | Altana Coatings & Sealants Gmbh | Packaging material with a barrier layer for gases |
| JP4304510B2 (en) * | 2004-02-16 | 2009-07-29 | 信越化学工業株式会社 | Flame retardant additive, emulsion type coating agent and flame retardant composition |
| DE102004014216A1 (en) * | 2004-03-23 | 2005-10-13 | Wacker-Chemie Gmbh | Crosslinkable compositions based on organosilicon compounds |
| DE102004025767A1 (en) * | 2004-05-26 | 2005-12-22 | Degussa Ag | Stable solutions of N-substituted aminopolysiloxanes, their preparation and use |
| DE102004037045A1 (en) * | 2004-07-29 | 2006-04-27 | Degussa Ag | Aqueous silane nanocomposites |
| DE102004037044A1 (en) * | 2004-07-29 | 2006-03-23 | Degussa Ag | Agent for equipping cellulose-based and / or starch-based substrates with water-repellent and, at the same time, fungus, bacteria, insect and algae-deficient properties |
| DE102004037043A1 (en) * | 2004-07-29 | 2006-03-23 | Degussa Ag | Block condensates of organofunctional siloxanes, their preparation, use and their properties |
| DE102004049427A1 (en) * | 2004-10-08 | 2006-04-13 | Degussa Ag | Polyether-functional siloxanes, polyethersiloxane-containing compositions, processes for their preparation and their use |
| DE102004053384A1 (en) | 2004-11-02 | 2006-05-04 | Degussa Ag | Liquid, viscous agent based on an organofunctional silane system for the production of weather-resistant protective coatings to prevent contamination of surfaces |
| JP4548591B2 (en) * | 2004-12-24 | 2010-09-22 | 信越化学工業株式会社 | Flame retardant resin composition |
| DE102005004872A1 (en) * | 2005-02-03 | 2006-08-10 | Degussa Ag | Aqueous emulsions of functional alkoxysilanes and their condensed oligomers, their preparation and use for surface treatment |
| DE102005004871A1 (en) * | 2005-02-03 | 2006-08-10 | Degussa Ag | Highly viscous aqueous emulsions of functional alkoxysilanes, their condensed oligomers, organopolysiloxanes, their preparation and their use for the surface treatment of inorganic materials |
| CN100343311C (en) * | 2005-06-16 | 2007-10-17 | 南京市化学工业研究设计院有限公司 | Vinyl trimethoxysilane oligomer preparation method |
| DE102006003956A1 (en) * | 2006-01-26 | 2007-08-02 | Degussa Gmbh | Production of a corrosion protection layer on a metal surface e.g. vehicle structure comprises applying a sol-gel composition to the metal surface, drying and/or hardening and applying a further layer and drying and/or hardening |
| DE102006003957A1 (en) * | 2006-01-26 | 2007-08-02 | Degussa Gmbh | Water-dilutable sol-gel for coating paper, cardboard, wood, presspahn, plastics, lacquer, stone, ceramics, metal or alloy or as primer is obtained by reacting glycidyloxypropylalkoxysilane, aqueous silica sol, organic acid and crosslinker |
| DE102006013090A1 (en) * | 2006-03-20 | 2007-09-27 | Georg-August-Universität Göttingen | Composite material made of wood and thermoplastic material |
| CN101437830B (en) * | 2006-06-20 | 2013-04-17 | 陶氏康宁公司 | Process for the preparation of alkoxysilanes with reduced halide content |
| DE102006059473A1 (en) | 2006-12-14 | 2008-06-19 | Henkel Kgaa | Silyl-containing mixture of prepolymers and their use |
| US8088853B2 (en) * | 2006-12-21 | 2012-01-03 | Millennium Inorganic Chemicals, Inc. | Polysiloxane modified titanium dioxide |
| ES2725499T3 (en) | 2007-04-20 | 2019-09-24 | Evonik Degussa Gmbh | Mixture containing an organosilicon compound and its use |
| US7915368B2 (en) | 2007-05-23 | 2011-03-29 | Bridgestone Corporation | Method for making alkoxy-modified silsesquioxanes |
| US8501895B2 (en) * | 2007-05-23 | 2013-08-06 | Bridgestone Corporation | Method for making alkoxy-modified silsesquioxanes and amino alkoxy-modified silsesquioxanes |
| DE102007038313A1 (en) * | 2007-08-14 | 2009-02-19 | Evonik Degussa Gmbh | Inorganically-modified polyester binder composition, process for its preparation and its use |
| DE102007038314A1 (en) * | 2007-08-14 | 2009-04-16 | Evonik Degussa Gmbh | Process for the controlled hydrolysis and condensation of epoxy-functional organosilanes and their condensation with further organofunctional alkoxysilanes |
| DE102007060334A1 (en) * | 2007-08-17 | 2009-02-19 | Evonik Degussa Gmbh | Silane-based and aqueous coating system, its preparation and use |
| DE102007040246A1 (en) | 2007-08-25 | 2009-02-26 | Evonik Degussa Gmbh | Radiation-curable formulations |
| DE102008007261A1 (en) | 2007-08-28 | 2009-03-05 | Evonik Degussa Gmbh | Aqueous silane systems based on bis (trialkoxysilylalkyl) amines |
| DE102007045186A1 (en) * | 2007-09-21 | 2009-04-09 | Continental Teves Ag & Co. Ohg | Residue-free, layer-forming, aqueous sealing system for metallic silane-based surfaces |
| US7851559B2 (en) * | 2007-11-13 | 2010-12-14 | Teknor Apex Company | Soft zero halogen flame retardant thermoplastic elastomers |
| US8097674B2 (en) | 2007-12-31 | 2012-01-17 | Bridgestone Corporation | Amino alkoxy-modified silsesquioxanes in silica-filled rubber with low volatile organic chemical evolution |
| ES2364790T3 (en) * | 2008-05-15 | 2011-09-14 | Evonik Degussa Gmbh | ELECTRONIC WRAPPING |
| DE102008001855A1 (en) * | 2008-05-19 | 2009-11-26 | Evonik Degussa Gmbh | Two-component composition for the production of flexible polyurethane gelcoats |
| DE102008040783A1 (en) | 2008-07-28 | 2010-02-04 | Evonik Degussa Gmbh | Composition for building protection applications based on alkylalkoxysiloxanes having improved beading properties |
| CN102131854A (en) | 2008-08-29 | 2011-07-20 | 赢创德固赛有限责任公司 | Method for using silanes and silane blends in wood-plastic composite manufacturing |
| DE102008041920A1 (en) | 2008-09-09 | 2010-03-11 | Evonik Degussa Gmbh | New catalysts for the crosslinking of functional silanes or functional siloxanes, especially with substrates |
| DE102008041918A1 (en) * | 2008-09-09 | 2010-03-11 | Evonik Degussa Gmbh | Silanol condensation catalysts for the crosslinking of filled and unfilled polymer compounds |
| DE102008041919A1 (en) * | 2008-09-09 | 2010-03-11 | Evonik Degussa Gmbh | Use of silicon-containing precursor compounds of an organic acid as a catalyst for crosslinking filled and unfilled polymer compounds |
| DE102009000614A1 (en) | 2009-02-04 | 2010-08-05 | Evonik Degussa Gmbh | Fluorine-free composition for water-repellent coating of surfaces with improved beading properties |
| DE102009002477A1 (en) | 2009-04-20 | 2010-10-21 | Evonik Degussa Gmbh | Quaternary amino functional, organosilicon compounds containing composition and their preparation and use |
| JP4893787B2 (en) * | 2009-07-23 | 2012-03-07 | 信越化学工業株式会社 | Organopolysiloxane and method for producing the same |
| DE102009045112A1 (en) | 2009-09-29 | 2011-03-31 | Evonik Degussa Gmbh | Mixture for cementitious materials with easy-to-clean properties |
| US8642691B2 (en) | 2009-12-28 | 2014-02-04 | Bridgestone Corporation | Amino alkoxy-modified silsesquioxane adhesives for improved metal adhesion and metal adhesion retention to cured rubber |
| JP5758979B2 (en) | 2010-04-01 | 2015-08-05 | エボニック デグサ ゲーエムベーハーＥｖｏｎｉｋ Ｄｅｇｕｓｓａ ＧｍｂＨ | Cement-containing mixture for materials with "easy to clean" properties by modification of uncured material with fluorine-containing actives |
| DE102011007137A1 (en) | 2011-04-11 | 2012-10-11 | Evonik Degussa Gmbh | Solution comprising organofunctional alkali siliconates, silicates and process for their preparation |
| DE102011086362A1 (en) | 2011-11-15 | 2013-05-16 | Evonik Industries Ag | A composition comprising block co-condensates of propyl-functional alkali silicates and silicates and processes for their preparation |
| DE102014206359A1 (en) | 2014-04-03 | 2015-10-08 | Evonik Degussa Gmbh | Low-VOC dialkyl-functional alkoxysiloxanes, processes and their use as hydrophobizing impregnating agents for mineral building materials |
| MX2016013185A (en) * | 2014-04-10 | 2017-01-16 | 3M Innovative Properties Co | Adhesion promoting and/or dust suppression coating. |
| WO2017157836A1 (en) | 2016-03-16 | 2017-09-21 | Construction Research & Technology Gmbh | Surface applied corrosion inhibitor |
| DK3243807T3 (en) | 2016-05-12 | 2019-03-18 | Evonik Degussa Gmbh | APPLICATION OF AURAL EMULSIONS ON THE BASIS OF PROPYLETHOXYSILANOLIGOMER AS ADDITIVES IN HYDRAULICALLY BINDING CEMENT MIXTURES TO REDUCE WASTE |
| KR102480348B1 (en) * | 2018-03-15 | 2022-12-23 | 삼성전자주식회사 | Pre-treatment composition before etching SiGe and method of fabricating a semiconductor device |
| CN116601127A (en) | 2020-12-18 | 2023-08-15 | 赢创运营有限公司 | Dilute stable aqueous compositions for bulk hydrophobization of inorganic building materials |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3037220A1 (en) * | 1980-10-02 | 1982-04-29 | Dynamit Nobel Ag, 5210 Troisdorf | STABLE AQUEOUS IMPREME SOLUTIONS MADE OF HYDROLLED ALKYLTRIAL COXISILANANE |
| US4950779A (en) * | 1989-12-04 | 1990-08-21 | General Electric Company | Nonaqueous method for making silicone oligomers |
| US5346968A (en) * | 1990-04-21 | 1994-09-13 | Basf Aktiengesellschaft | Oligosiloxanes and reinforced thermoplastic and ceramic materials obtainable therewith |
| US5112393A (en) * | 1990-10-09 | 1992-05-12 | Prosoco, Inc. | Method of rendering masonry materials water repellent with low voc organoalkoxysilanes |
| ES2120423T3 (en) * | 1991-06-08 | 1998-11-01 | Huels Chemische Werke Ag | BLENDS OF SILOXAN OLIGOMEROS IN THE FORM OF CHAIN AND CYCLICS, PROCEDURE FOR ITS MANUFACTURE, AS WELL AS ITS USE. |
| US5225510A (en) * | 1992-07-15 | 1993-07-06 | Dow Corning Corporation | Masonry treating composition and method |
| US5348760A (en) * | 1993-10-12 | 1994-09-20 | Aluminum Company Of America | Surface treated ceramic powders |
| US5543173A (en) * | 1993-10-12 | 1996-08-06 | Aluminum Company Of America | Surface treating aluminum trihydrate powders with prehydrolized silane |
| EP1136494A3 (en) * | 1994-03-31 | 2001-12-19 | Sivento Inc. | Method for preparation of stable water-borne silane compositions |
| DE4443824A1 (en) * | 1994-12-09 | 1996-06-13 | Huels Chemische Werke Ag | Organopolysiloxane-containing water-based compositions, processes for their preparation and their use |
| US5563231A (en) * | 1995-06-06 | 1996-10-08 | Bayer Corporation | Capped silanes and their application to textile substrates |
-
1996
- 1996-06-17 DE DE19624032A patent/DE19624032A1/en not_active Withdrawn
-
1997
- 1997-05-28 EP EP97108564A patent/EP0814110B1/en not_active Expired - Lifetime
- 1997-05-28 DE DE59703030T patent/DE59703030D1/en not_active Expired - Lifetime
- 1997-06-16 JP JP9158276A patent/JPH1059984A/en active Pending
- 1997-06-16 CA CA002207977A patent/CA2207977A1/en not_active Abandoned
- 1997-06-16 PL PL97320584A patent/PL320584A1/en unknown
- 1997-06-17 US US08/877,556 patent/US5932757A/en not_active Expired - Lifetime
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2000178449A (en) * | 1998-10-27 | 2000-06-27 | Degussa Huels Ag | Aminopropyl-functional siloxane oligomer |
| JP2012092106A (en) * | 1998-10-27 | 2012-05-17 | Evonik Degussa Gmbh | Aminopropyl-functional siloxane oligomer |
| JP2013028530A (en) * | 2002-04-26 | 2013-02-07 | Evonik Degussa Gmbh | Process for impregnating porous mineral support, and use of specific spray technology therefor |
| JP2006507375A (en) * | 2002-08-22 | 2006-03-02 | デグサ アクチエンゲゼルシャフト | Acts as a coupling agent for filled and peroxide crosslinked rubber compounds |
| JP4824310B2 (en) * | 2002-08-22 | 2011-11-30 | エボニック デグサ ゲーエムベーハー | Acts as a coupling agent for filled and peroxide crosslinked rubber compounds |
| JP2008537740A (en) * | 2005-03-24 | 2008-09-25 | 株式会社ブリヂストン | Silica-reinforced rubber compounding with low emission of volatile organic compounds (VOC) |
| US9403969B2 (en) | 2005-03-24 | 2016-08-02 | Bridgestone Corporation | Compounding silica-reinforced rubber with low volatile organic compound (VOC) emission |
| US8962746B2 (en) | 2007-12-27 | 2015-02-24 | Bridgestone Corporation | Methods of making blocked-mercapto alkoxy-modified silsesquioxane compounds |
| US9447244B2 (en) | 2007-12-27 | 2016-09-20 | Bridgestone Corporation | Methods of making blocked-mercapto alkoxy-modified silsesquioxane compounds |
| US9365700B2 (en) | 2007-12-31 | 2016-06-14 | Bridgestone Corporation | Amino alkoxy-modified silsesquioxane adhesives for improved metal adhesion and metal adhesion retention to cured rubber |
| US11401440B2 (en) | 2014-12-31 | 2022-08-02 | Bridgestone Corporation | Amino alkoxy-modified silsesquioxane adhesives for adhering steel alloy to rubber |
Also Published As
| Publication number | Publication date |
|---|---|
| US5932757A (en) | 1999-08-03 |
| DE19624032A1 (en) | 1997-12-18 |
| PL320584A1 (en) | 1997-12-22 |
| EP0814110A1 (en) | 1997-12-29 |
| DE59703030D1 (en) | 2001-04-05 |
| EP0814110B1 (en) | 2001-02-28 |
| CA2207977A1 (en) | 1997-12-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5932757A (en) | Mixture of oligomers of condensed alkylalkoxysilanes | |
| JP4259791B2 (en) | Oligomer mixture of n-propylethoxysiloxane, process for its production and use thereof | |
| JP4083413B2 (en) | Process for the continuous production of mixtures of organoalkoxysiloxanes, mixtures thereof and their use | |
| JP4970637B2 (en) | Aminopropyl functional siloxane oligomer | |
| JP4410878B2 (en) | Mixtures of linear and cyclic siloxane oligomers, their preparation and use | |
| EP0195936B1 (en) | Method for producing organosilicon polymers and the polymers prepared thereby | |
| JPH0422945B2 (en) | ||
| US5210168A (en) | Process for forming siloxane bonds | |
| JP2003201293A (en) | Aminoalkylalkoxysiloxane-containing mixture, method for producing the same, application of the same, and paint, lacquer and resin containing the same | |
| JPH09208827A (en) | Organosilicon compound, its production, cross-linkable composition containing the same, and sticky-substance-repellent coating film containing the same | |
| US9200013B2 (en) | Method for producing solids from alkali salts of silanols | |
| JP2004002299A (en) | Method for producing mixture of chain and cyclic siloxanes, mixture and use thereof | |
| US20130289190A1 (en) | Binder Composition | |
| JPH0633335B2 (en) | Method for producing organopolysiloxane | |
| JPH07228701A (en) | Method for producing silicone resin containing silicon atom-bonded hydrogen atom | |
| US2706723A (en) | Water repellent treatment for masonry and siloxane composition | |
| JPH0466271B2 (en) | ||
| JP2596706B2 (en) | Production method of organopolysiloxane resin | |
| CN107207732B (en) | Process for the preparation of siloxanols from metal salts of silanols | |
| US5516867A (en) | Modified hydrogen silsesquioxane resin | |
| CN106164012A (en) | Method for producing powder from alkali metal salt of silanol | |
| TW457275B (en) | Organopolysiloxane compounds cross-linkable by cleaving of alcohols to form elastomers | |
| JP2021530573A (en) | Method for preparing branched organopolysiloxane | |
| JP2599517B2 (en) | Method for producing organopolysiloxane | |
| JPH0931329A (en) | Polyorganosilyl silicate composition and method for producing the same |